Triethylamine → Ecgonine

Participants

Reaction Conditions

Reaction Steps

A solution of 1.93 g (4.5 mmole) of the above compound in 20 mL of dry tetrahydrofuran and 5 mL of 1,2-dimethoxylethane was treated with 0.52 g (2.5 mmole) of 1,3-dicyclohexylcarbodiimide. This mixture was stirred and heated at 45° C. for 72 hours. Then, triethylamine (0.6 mL), 4-dimethylaminopyridine (250 mg) and ecgonine hydrochloride (0.55 g, 2.4 mmole) were added, and the reaction was concentrated in vacuo to a dark, semi-solid residue which was taken up in a minimum of dichloromethane and applied atop a column packed with 60.0 g of Merck "60" silica gel. The column was eluted with a gradient of 20 to 40% of methanol in ethyl acetate. The homogeneous fractions showed an Rf on silica gel plates of 0.16 in 3:1 methanol/acetate containing 1% of NH4OH solution. There was obtained 230 mg of [4-(6-carbobenzyloxy-aminocaproyl) aminobenzoyl] ecgonine as an amorphous powder.

Provenance & Evidence